Pyrazole carboxanilide fungicide

ABSTRACT

Novel pyrazole-carboxanilides of the formula                    
     in which 
     X, Y, m and n are each as defined in the description, 
     a process for preparing these substances and their use for controlling undesirable microorganisms.

This application is a 371 of PCT/EP99/06149 filed Aug. 23, 1999.

FIELD OF THE INVENTION

The present invention relates to novel pyrazole-carboxanilides, to aprocess for their preparation and to their use for controllingundesirable microorganisms.

BACKGROUND OF THE INVENTION

It is already known that numerous carboxanilides have fungicidalproperties (compare WO 93/11 117, EP-A 0 545 099 and EP-A 0 589 301).Thus, N-(2-cyclohexyl)-1,3-dimethyl-5-fluoropyrazole-4-carboxanilide,N-(2-phenyl)-1,3-dimethyl-pyrazole-4-carboxanilide andN-[2-(2-fluoro-phenyl)]-1,3-dimethyl-pyrazole-4-carboxanilide can beused for controlling fungi. The activity of these substances is good,however, it is sometimes unsatisfactory at low application rates.

SUMMARY OF THE INVENTION

Pyrazole-carboxanilides of the formula

wherein m, n, X and Y are as described may be used for controllingundesirable microorganisms.

DETAILED DESCRIPTION

This invention, accordingly, provides novel pyrazole-carboxanilides ofthe formula

in which

a) m represents the number 0,

n represents the number 1 and

Y represents 2-chloro, 2-fluoro, 4-bromo, 2-methyl, 2-trifluoromethyl,3-trifluoromethyl,

represents nitro, cyano, hydroxyl, carboxyl, halogenoalkoxy having 1 to6 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 6carbon atoms and 1 to 5 halogen atoms, alkenyloxy having 2 to 8 carbonatoms, alkinyloxy having 2 to 8 carbon atoms, cycloalkyl having 3 to 8carbon atoms, carbalkoxy having 1 to 8 carbon atoms in the alkoxy moietyor alkoximinoalkyl having 1 to 6 carbon atoms in the alkoxy moiety and 1to 6 carbon atoms in the alkyl moiety,

 or

b) m represents the number 0,

n represents the number 2 or 3 and

Y represents halogen, nitro, cyano, hydroxyl, carboxyl, alkyl having 1to 8 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5halogen atoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 8carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5halogen atoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxyhaving 1 to 8 carbon atoms in the alkoxy moiety or alkoximinoalkylhaving 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atomsin the alkyl moiety,

 or

c) m represents the number 1,

X represents chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, alkylhaving 1 to 8 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and1 to 5 halogen atoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxyhaving 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1to 8 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to5 halogen atoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxyhaving 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms,carbalkoxy having 1 to 8 carbon atoms in the alkoxy moiety oralkoximinoalkyl having 1 to 6 carbon atoms in the alkoxy moiety and 1 to6 carbon atoms in the alkyl moiety,

n represents integers from 0 to 3 and

Y represents halogen, nitro, cyano, hydroxyl, carboxyl, alkyl having 1to 8 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5halogen atoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 8carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5halogen atoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxyhaving 1 to 8 carbon atoms in the alkoxy moiety or alkoximinoalkylhaving 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atomsin the alkyl moiety.

Furthermore, it has been found that pyrazole-carboxanilides of theformula (I) are obtained by reacting acyl halides of the formula

in which

Hal represents halogen with aniline derivatives of the formula

 in which

X, Y, m and n are each as defined above,

if appropriate in the presence of an acid binder and if appropriate inthe presence of a diluent.

Finally, it has been found that the novel pyrazole-carboxanilides of theformula (I) have very good microbicidal properties and can be used forcontrolling undesirable microorganisms, both in crop protection and inthe protection of materials.

Surprisingly, the pyrazole-carboxanilides of the formula (I) accordingto the invention have considerably better fungicidal activity thanN-(2-cyclohexyl)-1,3-dimethyl-5-fluoropyrazole-4-carboxanilide,N-(2-phenyl)-1,3-dimethyl-pyrazole-4-carboxanilide andN-[2-(2-fluoro-phenyl)]-1,3-dimethyl-pyrazole-4-carboxanilide, which arethe constitutionally most similar active compounds of the prior art ofthe same direction of action.

The formula (I) provides a general definition of thepyrazole-carboxanilides according to the invention.

Preference is given to compounds of the formula (I) in which

a) m represents the number 0,

n represents the number 1 and

Y represents 2-chloro, 2-fluoro, 4-bromo, 2-methyl, 2-trifluoromethyl,3-trifluoromethyl,

represents nitro, cyano, hydroxyl, carboxyl, halogenoalkoxy having 1 or2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 fluorine,chlorine and/or bromine atoms, alkenyloxy having 2 to 6 carbon atoms,alkinyloxy having 2 to 6 carbon atoms, cycloalkyl having 3 to 7 carbonatoms, carbalkoxy having 1 to 4 carbon atoms in the alkoxy moiety orrepresents alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxymoiety and 1 to 4 carbon atoms in the alkyl moiety,

 or

b) m represents the number 0,

n represents the number 2 or 3 and

Y represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl,carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 or 2carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkoxyhaving 1 to 6 carbon atoms, halogenoalkoxy having 1 or 2 carbon atomsand 1 to 5 fluorine, chlorine and/or bromine atoms, alkylthio having 1to 6 carbon atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to5 fluorine, chlorine and/or bromine atoms, alkenyloxy having 2 to 6carbon atoms, alkinyloxy having 2 to 6 carbon atoms, cycloalkyl having 3to 7 carbon atoms, carbalkoxy having 1 to 4 carbon atoms in the alkoxymoiety or represents alkoximinoalkyl having 1 to 4 carbon atoms in thealkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety,

 or

c) m represents the number 1,

X represents chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, alkylhaving 1 to 6 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and1 to 5 fluorine, chlorine and/or bromine atoms, alkoxy having 1 to 6carbon atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 6 carbonatoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 fluorine,chlorine, and/or bromine atoms, alkenyloxy having 2 to 6 carbon atoms,alkinyloxy having 2 to 6 carbon atoms, cycloalkyl having 3 to 7 carbonatoms, carbalkoxy having 1 to 4 carbon atoms in the alkoxy moiety orrepresents alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxymoiety and 1 to 4 carbon atoms in the alkyl moiety,

n represents integers from 0 to 3 and

Y represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl,carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 or 2carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkoxyhaving 1 to 6 carbon atoms, halogenoalkoxy having 1 or 2 carbon atomsand 1 to 5 fluorine, chlorine and/or bromine atoms, alkylthio having 1to 6 carbon atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to5 fluorine, chlorine and/or bromine atoms, alkenyloxy having 2 to 6carbon atoms, alkinyloxy having 2 to 6 carbon atoms, cycloalkyl having 3to 7 carbon atoms, carbalkoxy having 1 to 4 carbon atoms in the alkoxymoiety or represents alkoximinoalkyl having 1 to 4 carbon atoms in thealkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety.

Particular preference is given to compounds of the formula (I) in which

a) m represents the number 0,

n represents the number 1 and

Y represents 2-chloro, 2-fluoro, 4-bromo, 2-methyl, 2-trifluoromethyl,3-trifluoromethyl,

represents nitro, cyano, hydroxyl, carboxyl, difluoromethoxy,trifluoromethoxy, trifluoromethylthio, difluorochloromethylthio,allyloxy, propargyloxy, cyclopropyl, cyclopentyl, cyclohexyl,cycloheptyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl,ethoximinomethyl, methoximinoethyl or ethoximinoethyl,

 or

b) m represents the number 0,

n represents the number 2 or 3 and

Y represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl,carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl,i-butyl, tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl, methoxy, ethoxy, methylthio, difluoromethoxy,trifluoromethoxy, trifluoromethylthio, difluorochloromethylthio,allyloxy, propargyloxy, cyclopropyl, cyclopentyl, cyclohexyl,cycloheptyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl,ethoximinomethyl, methoximinoethyl or ethoximinoethyl,

 or

c) m represents the number 1,

X represents chlorine, bromine, nitro, cyano, hydroxyl, carboxyl,methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl,tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl, methoxy, ethoxy, methylthio, difluoromethoxy,trifluoromethoxy, trifluoromethylthio, difluorochloromethylthio,allyloxy, propargyloxy, cyclopropyl, cyclopentyl, cyclohexyl,cycloheptyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl,ethoximinomethyl, methoximinoethyl or ethoximinoethyl,

n represents integers from 0 to 3 and

Y represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl,carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl,i-butyl, tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl, methoxy, ethoxy, methylthio, difluoromethoxy,trifluoromethoxy, trifluoromethylthio, difluorochloromethylthio,allyloxy, propargyloxy, cyclopropyl, cyclopentyl, cyclohexyl,cycloheptyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl,ethoximinomethyl, methoximinoethyl or ethoximinoethyl.

The abovementioned definitions can be combined with one another asdesired. Moreover, individual definitions may not apply.

Using 1,3-dimethyl-5-fluoropyrazole-4-carbonyl chloride and2-(4-bromo-phenyl)-aniline as starting materials, the course of theprocess according to the invention can be illustrated by the formulascheme below.

The formula (II) provides a general definition of the acyl halidesrequired as starting, materials for carrying out the process accordingto the invention. In this formula, Hal preferably represents fluorine,chlorine or bromine.

The acyl halides of the formula (II) are known or can be prepared byknown processes (cf. WO 93/11 117 and EP-A 0 776 889).

The formula (III) provides a general definition of the anilinederivatives required as reaction components for carrying out the processaccording to the invention. In this formula, X, Y, m and n eachpreferably have those meanings which have already been mentioned inconnection with the description of the substances of the formula (I)according to the invention as being preferred for these radicals orthese indices.

The aniline derivatives of the formula (III) are known or can beprepared by known methods (cf. EP-A 0 545 099 and EP-A 0 589 301).

Suitable acid binders for carrying out the process according to theinvention are all inorganic and organic bases which are customary forsuch reactions. Preference is given to using alkaline earth metal oralkali metal hydroxides, such as sodium hydroxide, calcium hydroxide,potassium hydroxide, or else ammonium hydroxide, alkali metalcarbonates, such as sodium carbonate, potassium carbonate, potassiumbicarbonate, sodium bicarbonate, alkali metal or alkaline earth metalacetates, such as sodium acetate, potassium acetate, calcium acetate,and also tertiary amines, such as trimethylamine, triethylamine,tributylamine, N,N-dimethylaniline, pyridine N-methylpiperidine,N,N-dimethylaminopyridine, diazabicyclooctane (DABCO),diazabicyclononene (DBN) or diazabicycloundecene (DBU). However, it isalso possible to carry out the process without an additional acidbinder, or to use an excess of the amine component, so that itsimultaneously acts as acid binder.

Suitable diluents for carrying out the process according to theinvention are all customary inert organic solvents. Preference is givento using optionally halogenated aliphatic, alicyclic or aromatichydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene,dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride,dichloroethane or trichlorethane; ethers, such as diethyl ether,diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;nitrites, such as acetonitrile, propionitrile, n- or i-butyronitrile orbenzonitrile; amides, such as N,N-dimethyl-formamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; esters, such as methyl acetate or ethylacetate, sulphoxides, such as dimethyl sulphoxide, or sulphones, such assulpholane.

When carrying out the process according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the process is carried out at temperatures between 0° C. and 140° C.,preferably between 10° C. and 120° C.

The process according to the invention is generally carried out underatmospheric pressure. However, it is also possible to operate in eachcase under elevated or reduced pressure.

When carrying out the process according to the invention. in general 1mol or else an excess of the aniline derivative of the formula (III) andfrom 1 to 3 mol of acid binder are employed per mole of acyl halide ofthe formula (II). However, it is also possible to use other ratios ofthe reaction components. Work-up is carried out by customary methods. Ingeneral, the reaction mixture is admixed with water and the organicphase is separated off and, after drying, concentrated under reducedpressure. The residue that remains can, if appropriate, be freed of anyimpurities that may still be present, using customary methods. such aschromatography or recrystallization.

The compounds according to the invention have a potent microbicidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides are employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides are employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above are mentioned as examples, but not by wayof limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Altemaria species, such as, for example, Altemaria brassicae; and

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The active compounds according to the invention can be used withparticularly good results for controlling diseases in viticulture and infruit and vegetable growing, such as, for example against Venturia,Botrytis, Sclerobinia, Rhizoctonia, Uncinula, Sphaerotheca, Podosphaera,Altemaria and Colletotriclum species. Rice diseases, such as Pyriculariaand Pellicularia species are likewise controlled with good results.

The active compounds according to the invention are also suitable forincreasing the yield of crops. Moreover, they have reduced toxicity andare tolerated well by plants.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be adhesives, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably adhesives, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds or compositions according tothe invention preferably act against fungi, in particular moulds,wood-discolouring and wood-destroying fungi (Basidiomycetes), andagainst slime organisms and algae.

Microorganisms of the following genera may be mentioned as examples:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia. such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa, and

Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and micro-encapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Suitable liquidsolvents are essentially: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as highlydisperse silica, alumina and silicates. Suitable solid carriers forgranules are: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, or else syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks.Suitable emulsifiers and/or foam formers are: for example nonionic andanionic emulsifiers, such as polyoxyethylene fatty acid esters,polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or elseprotein hydrolysates. Suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in theirformulations, can also be employed in mixtures with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum, or to prevent the development ofresistance. In many cases, synergistic effects are obtained, i.e. theactivity of the mixture is greater than the activity of the individualcomponents.

Examples of co-components in mixtures are the following compounds:

Fungicides:

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-alminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazaili, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB), quinoxyfen,

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

(E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone-O-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

2-[(1-methylethyl)sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

3,5-dichloro-N-[cyano-[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl)-1-oxo-1H-indene-2-carbonitrile,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

8-hydroxyquinoline sulphate,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)oxy]-2,5-thiophenedicarboxylate,

cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

ethyl[(4-chlorophenyl)-azo]-cyanoacetate,

potassium hydrogen carbonate,

methanetetrathiol sodium salt,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

N-((6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine sodium salt,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

spiro[2H]-1-benzopyran-2,1′(3′H)-isobenzofuran]-3′-one,

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alphacypermethrin, alphamethrin, amitraz, avermectin, AZ60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC, bromophosA, bufencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demneton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, diflubenzuron, dimethoate, dimethylvinphos,diofenolan, disulfoton, docusat-sodium, dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole,etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

granulosis viruses,

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,

imidacloprid, isazophos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron,

omethoate, oxamyl, oxydemethon M,

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenophos, promecarb,propoxur, prothiofos, prothoate, pymetrozine, pyraclofos, pyresmethrin,pyrethrum, pyridaben, pyridathion, pyrimidifen, pyriproxyfen,

quinalphos,

ribavirin,

salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, thetacypermethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazarnate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii,

YI 5302,

zeta-cypermethrin, zolaprofos,

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropane carboxylate,

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

3-methylphenyl propylcarbamate,

4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

Bacillus thuringiensis strain EG-2348,

[2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

It is also possible to admix other known active compounds, such asherbicides or fertilizers and growth regulators.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. They are used in the customary manner, for example bypouring, spraying, atomizing, spreading, foaming, brushing on and thelike. It is further possible to apply the active compounds by theultra-low volume method or to inject the active compound formulation, orthe active compound itself, into the soil. The seed of the plants canalso be treated.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the type of application. In the treatment of partsof plants, the application rates of active compound are generallybetween 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. In thetreatment of seed, the application rates of active compound aregenerally between 0.001 and 50 g per kilogram of seed, preferablybetween 0.01 and 10 g per kilogram of seed. In the treatment of thesoil, the application rates of active compound are generally between 0.1and 10,000 g/ha, preferably between 1 and 5000 g/ha.

The compositions used for the protection of industrial materialsgenerally comprise an amount of 1 to 95%, preferably 10 to 75%, of theactive compounds.

The use concentrations of the active compounds according to theinvention depend on the species and the occurrence of the microorganismsto be controlled and on the composition of the material to be protected.The optimum rate of application can be determined by test series. Ingeneral, the use concentrations are in the range from 0.001 to 5% byweight, preferably 0.05 to 1.0% by weight, based on the material to beprotected.

The activity and the activity spectrum of the active compounds to beused according to the invention in the protection of materials, or ofthe compositions, concentrates or quite generally formulationspreparable therefrom, can be increased by, if appropriate, adding otherantimicrobially active compounds, fungicides, bactericides, herbicides,insecticides or other active compounds for broadening the activityspectrum or obtaining particular effects, such as, for example, theadditional protection against insects. These mixtures may have a broaderactivity spectrum than the compounds according to the invention.

The preparation and the use of the substances according to the inventionis illustrated by the examples below.

PREPARATION EXAMPLES

At room temperature, a solution of 2.5 g (0.01 mol) of2-(4-bromo-phenyl)-aniline in 30 ml of toluene is admixed with 1.0 g(0.01 mol) of triethylamine. At room temperature, 1.8 g (0.01 mol) of1,3-dimethyl-5-fluoro-pyrazole-4-carbonyl chloride are added withstirring to this mixture. After the addition has ended, the reactionmixture is stirred at room temperature for two hours and then pouredinto water. The mixture is extracted repeatedly with chloroform. Thecombined organic phases are dried over sodium sulphate, filtered andconcentrated under reduced pressure. The residue that remains is stirredwith diisopropyl ether. The resulting crystalline product is filteredoff with suction and dried. This gives 1.6 g (41.2% of theory) ofN-[2-(4-bromophcnyl)]-1,3-dimethyl-5-fluoro-pyrazole-4-carboxanilide inthe form of a solid of melting point 127° C.

The pyrazole-carboxanilides of the formula (I) listed in the table beloware likewise prepared in the manner described above.

TABLE 1 (I)

Ex- ample No.

Physical constant 2

m.p. 100° C. 3

¹H-NMR* δ = 2.34 (3H) 3.61 (3H) 4

m.p. 103° C. 5

m.p. 113° C. 6

m.p. 127° C. 7

m.p. 89° C. 8

¹H-NMR* δ = 2.38 (3H) 2.45 (3H) 9

m.p. 116° C. 10

m.p. 145° C. 11

m.p. 151° C. 12

m.p. 154° C. 13

m.p. 176° C. 14

m.p. 153° C. 15

m.p. 169° C. 16

m.p. 144° C. 17

m.p. 177° C. 18

m.p. 154° C. 19

oil 20

m.p. 168° C. 21

m.p. 169° C. 22

m.p. 168° C. 23

24

m.p. 172° C. *The ¹H-NMR spectra were recorded in deuterochloroform(CDCl₃) using tetramethylsilane (TMS) as internal standard. What isstated is the chemical shift as δ value in ppm.

USE EXAMPLES Example A

Podosphaera test (apple)/protective Solvent: 47 parts by weight ofacetone Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of the causative organism of apple mildew Podosphaeraleucotricha. The plants are then placed in a greenhouse at about 23° C.and a relative atmospheric humidity of about 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE A Podosphaera test (apple)/protective Application rate of activecompound Efficacy Active compound in g/ha in % According to theinvention: (1) 100 100

(2) 100 96

(4) 100 97

(5) 100 99

(8) 100 98

(9) 100 100

Example B

Sphaerotheca test (cucumber)/protective Solvent: 47 parts by weight ofacetone Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. Afier thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Sphaerotheca fuliginea. The plants are then placedat about 23° C. and a relative atmospheric humidity of about 70% in agreenhouse.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE B Sphaerotheca test (cucumber)/protective Application rate ofactive compound Efficacy Active compound in g/ha in % According to theinvention: (1) 100 95

(9) 100 94

Example C

Venturia test (apple)/protective Solvent: 47 parts by weight of acetoneEmulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the causative organism of apple scab Venturiainaequalis and then remain in an incubation cabin at 20° C. and 100%relative atmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE C Venturia test (apple)/protective Application rate of activecompound Efficacy Active compound in g/ha in % According to theinvention: (1) 100 100

(8) 100 100

(9) 100 97

Example D

Erysiphe test (barley)/protective

Solvent: 48.8 parts by weight of N,N-dimethylformamide Emulsifier:  1.2parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young cereal plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with spores of Erysiphegraminis f. sp. hordei. The plants are then placed in a greenhouse at70% relative atmospheric humidity and a temperature of 18° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE D Erysiphe test (barley)/protective Application rate of activecompound Efficacy Active compound in g/ha in % (2) 750 90

(1) 750 100

(16) 750 94

(17) 750 100

Example E

Pyrenophora teres test (barley)/protective Solvent: 25 parts by weightof N,N-dimethylacetamide Emulsifier: 0.6 part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Pyrenophora teres. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of about 80%.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE E Pyrenophora teres test (barley)/protective Application rate ofactive compound Efficacy Active compound in g/ha in % (1) 250 100

(8) 250 100

(9) 250 100

(17) 250 100

What is claimed is:
 1. A pyrazole-carboxanilide of the formula

wherein a) m represents the number 0, n represents the number 1 and Yrepresents 2-chloro, 2-fluoro, 4-bromo, 2-methyl, 2-trifluoromethyl,3-trifluoromethyl,  or represents nitro, cyano, hydroxyl, carboxyl,halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms,halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms,alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having 2 to 8 carbonatoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxy having 1 to 8carbon atoms in the alkoxy moiety or alkoximinoalkyl having 1 to 6carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkylmoiety,  or b) m represents the number 0, n represents the number 2 or 3and Y represents halogen, nitro, cyano, hydroxyl, carboxyl, alkyl having1 to 8 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5halogen atoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 8carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5halogen atoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxyhaving 1 to 8 carbon atoms in the alkoxy moiety or alkoximinoalkylhaving 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atomsin the alkyl moiety,  or c) m represents the number 1, X representschlorine, bromine, nitro, cyano, hydroxyl, carboxyl, alkyl having 1 to 8carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5halogen atoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 8carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5halogen atoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxyhaving 1 to 8 carbon atoms in the alkoxy moiety or alkoximinoalkylhaving 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atomsin the alkyl moiety, n represents integers from 0 to 3 and Y representshalogen, nitro, cyano, hydroxyl, carboxyl, alkyl having 1 to 8 carbonatoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogenatoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having 1 to 6carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 8 carbonatoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogenatoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having 2 to 8carbon atoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxy having 1to 8 carbon atoms in the alkoxy moiety or alkoximinoalkyl having 1 to 6carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkylmoiety.
 2. A pyrazole-carboxanilide of the formula (I) according toclaim 1, wherein a) m represents the number 0, n represents the number 1and Y represents 2-chloro, 2-fluoro, 4-bromo, 2-methyl,2-trifluoromethyl, 3-trifluoromethyl,  or represents nitro, cyano,hydroxyl, carboxyl, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5fluorine, chlorine and/or bromine atoms, halogenoalkylthio having 1 or 2carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,alkenyloxy having 2 to 6 carbon atoms, alkinyloxy having 2 to 6 carbonatoms, cycloalkyl having 3 to 7 carbon atoms, carbalkoxy having 1 to 4carbon atoms in the alkoxy moiety or represents alkoximinoalkyl having 1to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety,  or b) m represents the number 0, n represents the number2 or 3 and Y represents fluorine, chlorine, bromine, nitro, cyano,hydroxyl, carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkylhaving 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromineatoms, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 or 2carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 or 2carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,alkenyloxy having 2 to 6 carbon atoms, alkinyloxy having 2 to 6 carbonatoms, cycloalkyl having 3 to 7 carbon atoms, carbalkoxy having 1 to 4carbon atoms in the alkoxy moiety or represents alkoximinoalkyl having 1to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety,  or c) m represents the number 1, X represents chlorine,bromine, nitro, cyano, hydroxyl, carboxyl, alkyl having 1 to 6 carbonatoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine,chlorine and/or bromine atoms, alkoxy having 1 to 6 carbon atoms,halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorineand/or bromine atoms, alkylthio having 1 to 6 carbon atoms,halogenoalkylthio having 1 or 2 carbon atoms or 1 to 5 fluorine,chlorine, and/or bromine atoms, alkenyloxy having 2 to 6 carbon atoms,alkinyloxy having 2 to 6 carbon atoms, cycloalkyl having 3 to 7 carbonatoms, carbalkoxy having 1 to 4 carbon atoms in the alkoxy moiety orrepresents alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxymoiety and 1 to 4 carbon atoms in the alkyl moiety, n representsintegers from 0 to 3 and Y represents fluorine, chlorine, bromine,nitro, cyano, hydroxyl, carboxyl, alkyl having 1 to 6 carbon atoms,halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorineand/or bromine atoms, alkoxy having 1 to 6 carbon atoms, halogenoalkoxyhaving 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromineatoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,alkenyloxy having 2 to 6 carbon atoms, alkinyloxy having 2 to 6 carbonatoms, cycloalkyl having 3 to 7 carbon atoms, carboalkoxy having 1 to 4carbon atoms in the alkoxy moiety or represents alkoximinoalkyl having 1to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety.
 3. A pyrazole-carboxanilide according to claim 1, havingthe formula


4. A pyrazole-carboxanilide according to claim 1, having the formula


5. A pyrazole-carboxanilide according to claim 1, having the formula


6. A process for preparing pyrazole-carboxanilides of the formula (I)according to claim 1, comprising the step of reacting acyl halides ofthe formula

wherein Hal represents halogen, with aniline derivatives of the formula

 wherein X, Y, m and n are each as defined in claim
 1. 7. A compositionfor controlling undesirable microorganisms, comprising one or morepyrazole-carboxanilide of the formula (I) according to claim 1, inaddition to extenders and/or surfactants.
 8. A method for controllingundesirable microorganisms, comprising the step of applying one or morepyrazole-carboxanilides of the formula (I) according to claim 2 to themicroorganisms and/or their habitat.
 9. A method for controllingundesirable microorganisms, comprising the step of applying one or morepyrazole-carboxanilides of the formula (I) according to claim 1 to themicroorganisms and/or their habitat.
 10. A process for preparingcompositions for controlling undesirable microorganisms, comprising thestep of mixing one or more pyrazole-carboxanilides of the formula (I)according to claim 1 with extenders and/or surfactants.
 11. A processaccording to claim 6, wherein the step of reacting acyl halides withaniline derivatives occurs in the presence of an ingredient selectedfrom the group consisting of acid binders, diluents and mixturesthereof.
 12. A pyrazole-carboxanilide of the formula (I) according toclaim 1, wherein m represents the number 0, n represents the number 1and Y represents 2-chloro, 2-fluoro, 4-bromo, 2-methyl,2-trifluoromethyl, 3-trifluoromethyl, or represents nitro, cyano,hydroxyl, carboxyl, difluoromethoxy, trifluoromethoxy,trifluoromethylthio, difluorochloromethylthio, allyloxy, propargyloxy,cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl orethoximinoethyl.
 13. A pyrazole-carboxanilide of the formula (I)according to claim 1, wherein m represents the number 0, n representsthe number 2 or 3 and Y represents fluorine, chlorine, bromine, nitro,cyano, hydroxyl, carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl,sec-butyl, i-butyl, tert-butyl, trichloromethyl, trifluoromethyl,difluoromethyl, difluorochloromethyl, methoxy, ethoxy, methylthio,difluoromethoxy, trifluoromethoxy, trifluoromethylthio,difluorochloromethylthio, allyloxy, propargyloxy, cyclopropyl,cyclopentyl, cyclohexyl, cycloheptyl, methoxycarbonyl, ethoxycarbonyl,methoximinomethyl, ethoximinomethyl, methoximinoethyl orethoximinoethyl.
 14. A pyrazole-carboxanilide of the formula (I)according to claim 1, wherein m represents the number 1, X representschlorine, bromine, nitro, cyano, hydroxyl, carboxyl, methyl, ethyl,n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl, tert-butyl,trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl,methoxy, ethoxy, methylthio, difluoromethoxy, trifluoromethoxy,trifluoromethylthio, difluorochloromethylthio, allyloxy, propargyloxy,cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl orethoximinoethyl, n represents integers from 0 to 3 and Y representsfluorine, chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, methyl,ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl, tert-butyl,trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl,methoxy, ethoxy, methylthio, difluoromethoxy, trifluoromethoxy,trifluoromethylthio, difluorochloromethylthio, allyloxy, propargyloxy,cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl orethoximinoethyl.